Methanol → 9H-Fluoren-9-ylmethyl N-[(1S)-1-formyl-3-methylbutyl]carbamate

HRID 2380574Notes

Reaction equation

HRID 2380574 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH:5][C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7].C(=O)=O.CC(C)=O.[H-].C([Al+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1>[NH:5]([C:6]([O:8][CH2:9][CH:10]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[C@H:4]([CH:3]=[O:2])[CH2:23][CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 11474085HCID 11474085, compoundHCID 18522661Acetone cardice2×HCID 21225700Diisobutylaluminumhydride2×

Product 1

HCID 100427009H-Fluoren-9-ylmethyl N-[(1S)-1-formyl-3-methylbutyl]carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Fmoc-Leucine methyl ester (35 g, 134 mmoles) in dry toluene (250 ml) under N2 is cooled with dry ice/acetone, and 150 ml of 25 % di-isobutyl-aluminum hydride in toluene are added over 30 mins. The mixture is stirred for 20 min in a bath of dry ice/acetone after the addition of the di-isobutyl aluminum hydride, then methanol (15 ml) is added cautiously. The mixture is poured into 1000 ml ice-cold water, shaken and filtered. The toluene is separated and the aqueous phase re-extracted with ether (3×300 ml). Toluene and ether extracts are combined and dried over Na2SO4. The resulting oil is passed rapidly though a silica gel column (3×50 cm) in 1500 ml 15% EtOAc/petrol. The Fmoc-Leu-CHO is obtained as a solid (27.6 g).

Workup

  1. additionare added over 30 mins
  2. filtrationfiltered
  3. customThe toluene is separated
  4. extractionthe aqueous phase re-extracted with ether (3×300 ml)
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-bf39825edad44ae3ad4bfbdcb660ee69
Source dataset
uspto-grants-1994_11
Patent number
US05369094

Reaction notes

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