Hydrochloric Acid → (3R)-3-(tert-butyldiphenylsilyloxy)pyrrolidine hydrochloride

HRID 546543Notes

Reaction equation

HRID 546543 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)C1C=CC=CC=1.[ClH:31].[H][H]>CO.[PdH2]>[ClH:31].[C:27]([Si:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[O:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 57432600(3R)-1-Benzyl-3-(tert-butyldiphenylsilyloxy)pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 66786051(3R)-3-(tert-butyldiphenylsilyloxy)pyrrolidine hydrochloride

Reagents, catalysts & solvents 2

HCID 13628823Pd(II)-hydrideCatalystHCID 887MethanolSolvent

Procedure

(3R)-1-Benzyl-3-(tert-butyldiphenyl-silyloxy)pyrrolidine (1.18 g) was dissolved in methanol (12 ml), 1N hydrochloric acid (240 μl) and palladium hydride (221 mg) were added, and hydrogen was introduced to conduct catalytic reduction under normal pressure at room temperature for 4.5 hours. The catalyst was removed by filtration, and the filtrate was concentrated to solid under reduced pressure to obtain crude (3R)-3-(tert-butyldiphenyl-silyloxy)pyrrolidine hydrochloride (984 mg).

Workup

  1. customat room temperature
  2. customfor 4.5 hours
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated to solid under reduced pressure

Sources & evidence

ORD record
ord-82fa1ca728e84f1d980b968f38f2a5a1
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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