Dimethylamine → Tert-butyl (1r)-2-(dimethylamino)-1-((phenylthio)methyl)ethylcarbamate

HRID 2356045Notes

Reaction equation

HRID 2356045 reaction equation
[CH:1]([C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH3:20][NH:21][CH3:22].C1COCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:20][N:21]([CH3:22])[CH2:1][C@@H:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 11708946Tert-butyl (1r)-1-formyl-2-(phenylthio)ethylcarbamate

Product 1

HCID 91045570Tert-butyl (1r)-2-(dimethylamino)-1-((phenylthio)methyl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 134A (1.25 g, 4.44 mmol), 2M dimethylamine in THF (2.7 mL, 5.4 mmol), and NaBH(OAc)3 (1.32 g, 6.22 mmol) in dichloromethane at room temperature was stirred for 18 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 311 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9925554f161e4df8876e6bb09026e18e
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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