Sodium cyanoborohydride → N-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-(3-chlorophenyl)ethanamine

HRID 1901221Notes

Reaction equation

HRID 1901221 reaction equation
[Si:1]([O:8][C@H:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:19][C@H:20]([CH3:34])[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>CO>[CH3:33][O:32][C:30]([CH2:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C@H:20]([NH:19][CH2:10][C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH3:34])=[CH:24][CH:25]=1)=[O:31]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 11129841(R)-2-[(tert-Butyldimethylsilyl)oxy]-2-(3-chlorophenyl)acetaldehydeHCID 22867083Methyl 4-[2(R)-amino-1-propoxy]phenylacetate

Product 1

HCID 22873128N-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-(3-chlorophenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Preparation 29, but using 5.2 g of (R)-α-t-butyl-dimethylsilyloxy-α-(3-chlorophenyl)acetaldehyde (prepared as described in Preparation 49), 4.24 g of methyl 4-[2(R)-amino-1-propoxy]phenylacetate (prepared as described in Preparation 27), 50 ml of absolute methanol and 3.4 g of sodium cyanoborohydride, the title compound was obtained having an Rf=0.20 (thin layer chromatography over silica gel, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customthat described in Preparation 29

Sources & evidence

ORD record
ord-2c2a0dde8d27460bb9d3947acb4a6707
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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