Sodium triacetoxyborohydride → cis-1,1-Dimethylethyl ({(3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1 (2h)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamate

HRID 657136Notes

Reaction equation

HRID 657136 reaction equation
[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:12][NH:11][CH2:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8]1)([CH3:4])[CH3:3].[F:24][C:25]1[CH:34]=[C:33]2[C:28]([CH:29]=[CH:30][C:31](=[O:38])[N:32]2[CH2:35][CH:36]=O)=[CH:27][CH:26]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)(Cl)Cl>[CH3:4][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][C@H:7]1[CH2:12][N:11]([CH2:36][CH2:35][N:32]2[C:33]3[C:28](=[CH:27][CH:26]=[C:25]([F:24])[CH:34]=3)[CH:29]=[CH:30][C:31]2=[O:38])[CH2:10][C@@H:9]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8]1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehydeHCID 131729313cis-1,1-Dimethylethyl [((3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate

Product 1

HCID 131729314cis-1,1-Dimethylethyl ({(3rs,5rs)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-[2-(7-fluoro-2-oxo-1 (2h)-quinolinyl)ethyl]-3-piperidinyl}methyl)carbamateYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To cis-1,1-dimethylethyl [((3RS,5RS)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-3-piperidinyl)methyl]carbamate (350 mg; 1.0 mmol) in MeOH (2 ml) and CHCl3 (8 ml) was added (7-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde (for a preparation see Example 2(d) (200 mg; 1.0 mmol) and the reaction was allowed to stir at room temperature under N2 for 8 hours. Na(OAc)3BH (530 mg; 2.5 mmol) was added and the reaction was allowed to stir at room temperature under nitrogen for an additional 14 hours. The solvents were removed and the crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (415 mg; 78%) as a colorless oil.

Workup

  1. stirringto stir at room temperature under nitrogen for an additional 14 hours
  2. customThe solvents were removed
  3. customthe crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

Sources & evidence

ORD record
ord-dbcc701df83a449d963589d47d0720c7
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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