Diisobutylaluminum hydride → Tert-butyl (1r)-1-formyl-2-(phenylthio)ethylcarbamate

HRID 2356044Notes

Reaction equation

HRID 2356044 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>ClCCl>[CH:18]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:19]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

Product 1

HCID 11708946Tert-butyl (1r)-1-formyl-2-(phenylthio)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 133A (8.1 g, 26.0 mmol) in dichloromethane at −78° C. was treated with 1M DIBAL-H in dichloromethane (52 mL, 52 mmol), stirred for 3 hours, quenched with methanol (20 mL), and poured into saturated NaH2PO4. The mixture was extracted with ethyl acetate (3×300 mL), and the combined extracts were dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (ESI(−)) m/e 280 (M−H)−.

Workup

  1. customquenched with methanol (20 mL)
  2. additionpoured into saturated NaH2PO4
  3. extractionThe mixture was extracted with ethyl acetate (3×300 mL)
  4. dry with materialthe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-13461c6cfdce4b58a24309bc7065a057
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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