Sodium cyanoborohydride → N-[2-(4-methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

HRID 1901213Notes

Reaction equation

HRID 1901213 reaction equation
[Si:1]([O:8][C@H:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:18][C@@H:19]([CH3:33])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:23]=1.C([BH3-])#N.[Na+]>CO>[CH3:32][O:31][C:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C@@H:19]([NH:18][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:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:33])=[CH:23][CH:24]=1)=[O:30]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 10933947(R)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehydeHCID 22867084Methyl 4-[2(S)-amino-1-propoxy]phenylacetate

Product 1

HCID 22867087N-[2-(4-methoxycarbonylmethylphenoxy)-1(S)-methylethyl]-2(R)-t-butyldimethylsilyloxy-2-phenylethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Preparation 29, but using 750 mg of (R)-α-(t-butyldimethylsilyloxy)-α-phenylacetaldehyde (prepared as described in Preparation 25), 920 mg of methyl 4-[2(S)-amino-1-propoxy]phenylacetate (prepared as described in Preparation 28), 10 ml of absolute methanol and 500 mg of sodium cyanoborohydride, the title compound was obtained.

Workup

  1. customthat described in Preparation 29

Sources & evidence

ORD record
ord-4b3a959b8daf425785ca797d7f5b5d54
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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