Hydrochloric Acid → HCID 86604471, compound

HRID 1858763Notes

Reaction equation

HRID 1858763 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH:24]([OH:25])[CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH:20]2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41]COCC[Si](C)(C)C)=[CH:37][CH:36]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(Cl)Cl>CO>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]2[CH:24]([OH:25])[CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][CH:20]2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=2)=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 86604472HCID 86604472, compound

Product 1

HCID 86604471HCID 86604471, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

(β) A solution of 2.16 g (3.113 mmol) of tert-butyl (3RS,4SR,5SR)-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-hydroxy-3-[4-(2-trimethylsilanyl-ethoxymethoxy)-benzyloxy]-piperidine-1-carboxylate in 50 ml of methanol was treated with 2.02 ml (4.046 mmol) of an anhydrous 2M hydrogen chloride solution in methanol and stirred at room temperature for 2 hours. Subsequently, the mixture was treated with 100 ml of a 95:5 mixture of methylene chloride and methanol (extracted against 5 volume % of a saturated aqueous ammonia solution) and the solution was evaporated on a rotary evaporator at 30° C. The white solid (2.17 g) was thereupon chromatographed on silica gel using a 4:1 mixture of methylene chloride and ethyl acetate as the eluent. There were obtained 780 mg (45% of theory) of tert-butyl (3RS,4SR,5SR)-4-[4-(3-benzyloxy-propoxy)-phenyl]-5-hydroxy-3-(4-hydroxy-benzyloxy)-piperidine-1-carboxylate in the form of a colourless oil; MS: 581 (M+NH4)+.

Workup

  1. extractionextracted against 5 volume % of a saturated aqueous ammonia solution) and the solution
  2. customwas evaporated on a rotary evaporator at 30° C
  3. customThe white solid (2.17 g) was thereupon chromatographed on silica gel using
  4. additiona 4:1 mixture of methylene chloride and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-eb049de833084a45903246061d21142e
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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