Boron tribromide → p-[(1RS,2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide

HRID 580018Notes

Reaction equation

HRID 580018 reaction equation
S(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]1[C:25]2[C:20](=[CH:21][C:22]([O:26]C)=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH:17]1[C:28]1[CH:38]=[CH:37][C:31]([C:32]([N:34]([CH3:36])[CH3:35])=[O:33])=[CH:30][CH:29]=1)(C)(=O)=O.Br.[CH2:40]([S:46]C(=N)N)[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].B(Br)(Br)Br>CN(C)C=O>[CH2:40]([S:46][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=2)[CH2:19][CH2:18][CH:17]1[C:28]1[CH:29]=[CH:30][C:31]([C:32]([N:34]([CH3:35])[CH3:36])=[O:33])=[CH:37][CH:38]=1)[CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 12387367(Hexylsulfanyl)methanimidamide hydrobromideHCID 20135523p-[(1RS,2RS)-1-(10-mesyloxydecyl)-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide

Product 1

HCID 20135542p-[(1RS,2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Aqueous 1ON-sodium hydroxide solution (0.08 ml.) was added to a solution of p-[(1RS,2RS)-1-(10- mesyloxydecyl)-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide (0.107 g.) and S-n-hexylisothiourea hydrobromide (0.097 g.) in dimethylformamide (5 ml.) and the mixture was stirred at laboratory temperature for 2 hours and then evaporated to dryness. Water (5 ml.) was added to the residue and the mixture was extracted three times with diethyl ether (10 ml. each time). The combined extracts were dried and evaporated to dryness and the residue was purified by chromatography on a silica gel column using initially cyclohexane and then toluene as eluent. The product thus obtained was demethylated with boron tribromide by a similar process to that described in the second paragraph of Example 1, and the product was purified by chromatography on a silica gel column using a 4:4 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained as an oil p-[(1RS,2RS)-1-(10-hexylthiodecyl)-6-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-N,N-dimethylbenzamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. customevaporated to dryness
  2. additionWater (5 ml.) was added to the residue
  3. extractionthe mixture was extracted three times with diethyl ether (10 ml
  4. customThe combined extracts were dried
  5. customevaporated to dryness
  6. customthe residue was purified by chromatography on a silica gel column
  7. customThe product thus obtained
  8. customthe product was purified by chromatography on a silica gel column
  9. additiona 4:4 v/v mixture of toluene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-74133b3685fb4c78a093ccabb6f89678
Source dataset
uspto-grants-1988_06
Patent number
US04751240

Reaction notes

Loading…