Hydrochloric Acid → HCID 86604469, compound

HRID 1858762Notes

Reaction equation

HRID 1858762 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37]COCC[Si](C)(C)C)=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15]([C:46]([O-:48])=[O:47])[CH2:14]1.Cl.C(Cl)Cl>CO>[OH:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][O:29][CH2:28][CH2:27][CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH:18]2[CH2:17][CH2:16][N:15]([C:46]([O:48][C:2]([CH3:11])([CH3:3])[CH3:1])=[O:47])[CH2:14][CH:13]2[O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 22127469HCID 22127469, compound

Product 1

HCID 86604469HCID 86604469, compoundYield 160.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 50 mg (0.069 mmol) of 3-(naphthalen-2-ylmethoxy)-4-(4-{3-[2-(2-trimethylsilanyl-ethoxymethoxy)-benzyloxy]-propoxy}-phenyl)-piperidine-1-carboxylate in 0.5 ml of methanol was cooled to 0° C. under argon and treated with 69 μl (0.138 mmol) of a 2N solution of hydrogen chloride in methanol. Subsequently, the mixture was left to warm to room temperature and was stirred for a further one hour. For the working-up, the reaction solution was treated with a 95:5 mixture of methylene chloride and methanol (extracted against 5 vol. % saturated ammonia) and evaporated to dryness under reduced pressure. For purification, the residue was chromatographed on silica gel using a 3:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 33.1 mg (81% of theory) of tert-butyl (3RS,4RS)-4-{4-[3-(2-hydroxy-benzyloxy)-propoxy]-phenyl}-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless oil; MS: 598 (M+H)+.

Workup

  1. waitSubsequently, the mixture was left
  2. customevaporated to dryness under reduced pressure
  3. customFor purification
  4. customthe residue was chromatographed on silica gel using
  5. additiona 3:1 mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-6dbad136a82c48f2bdb6c08087c0d7bd
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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