Methanol → HCID 18631395, compound

HRID 745465Notes

Reaction equation

HRID 745465 reaction equation
C[O:2][C:3](=O)[C@H:4]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:5]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)=O.CO>C1(C)C=CC=CC=1.CCOCC>[C:17]([O:16][C:14]([NH:13][C@@H:5]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C@@H:4]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:3]=[O:2])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 887MethanolHCID 8025Ethyl formateHCID 13882365HCID 13882365, compoundHCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 18631395HCID 18631395, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 980 mg. (S)-3-t-butoxycarbonylamino-(R)-2-benzyloxy-4-cyclohexylbutyric acid methyl ester (Ii) in dry toluene (5 ml.) was cooled and stirred at -78° C. while a solution of diisobutylaluminum hydride (DIBAL-H, 6.05 ml.) was added dropwise so that the temperature did not exceed -65° C. 15 minutes after completion of the DIBAL-H addition dry ethyl formate (0.48 ml.) was added dropwise followed by dry methanol (0.6 ml.), stirring being then continued another 15 minutes at -78° C. whereupon a 50% aqueous solution of Rochelle salts was added (10 ml.) followed by ether (50 ml.), and the mixture was brought to room temperature. The emulsion was allowed to separate and the ether layer was washed with brine, dried and concentrated to give 880 mg. (97%) of the title aldehyde which was used without further purification.

Workup

  1. additionwas added dropwise so that the temperature
  2. customdid not exceed -65° C
  3. additionwas added dropwise
  4. additionwas added (10 ml.)
  5. customwas brought to room temperature
  6. customto separate
  7. washthe ether layer was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customto give 880 mg
  11. custom(97%) of the title aldehyde which was used without further purification

Sources & evidence

ORD record
ord-63bff55fadec492f86f4721af729c548
Source dataset
uspto-grants-1986_07
Patent number
US04599198

Reaction notes

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