Isopropylamine → (3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158347Notes

Reaction equation

HRID 1158347 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]=O)[C@H:10]([C:15]([CH3:23])([CH3:22])[O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]([NH2:27])([CH3:26])[CH3:25].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:27][CH:24]([CH3:26])[CH3:25])[C@H:10]([C:15]([CH3:23])([CH3:22])[O:16][SiH2:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 131728359(3S*,4S*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131728361(3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (3S,4S)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (7.7 g, 22.41 mmol) and isopropylamine (5.78 mL, 67.24 mmol) in 1,2-dichloroethane (200 mL) is stirred 25 min before the addition of NaBH(OAc)3 (11.88 g, 56.03 mmol). The solution is stirred for 5 h, then diluted with CH2Cl2 and washed with an aqueous saturated solution of NaHCO3. The aqueous layer is back extracted twice with CH2Cl2 and the combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude material is used in the next step without further purification. TLC, Rf (CH2Cl2/MeOH 9:1)=0.39. MS (LC-MS): 387.2 [M+H]+.

Workup

  1. washwashed with an aqueous saturated solution of NaHCO3
  2. extractionThe aqueous layer is back extracted twice with CH2Cl2
  3. dry with materialthe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is used in the next step without further purification

Sources & evidence

ORD record
ord-b550a920945a4e07ac1aeb1755e4e11d
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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