Acetone → HCID 86596897, compound

HRID 1374358Notes

Reaction equation

HRID 1374358 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@H:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C@@H:5]([N:13]2[CH2:17][CH2:16][C@H:15]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[C:14]2=[O:29])[CH2:4][CH2:3]1.[CH3:30][C:31]([CH3:33])=O.[BH-](OC(C)=O)(OC(C)=O)O[C:36](C)=O.[Na+].C=O>C(Cl)Cl>[CH2:22]([O:21][C:19]([NH:18][C@H:15]1[CH2:16][CH2:17][N:13]([C@H:5]2[CH2:4][CH2:3][C@@H:2]([N:1]([CH:31]([CH3:33])[CH3:30])[CH3:36])[CH2:7][C@@H:6]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:14]1=[O:29])=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86596898HCID 86596898, compound

Product 1

HCID 86596897HCID 86596897, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (1S,2S,5R)-ethyl 5-amino-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexanecarboxylate from step 2 in CH2Cl2 (10 ml) was treated with acetone (1 ml) and NaBH(OAc)3 (1.7 g, 8 mmol) and stirred at room temperature overnight. A solution of 37% aq formaldehyde (2 ml) was added and stirred at room temperature for 1 h. The solution was diluted with CH2Cl2 (50 ml) and washed with 1 N NaOH, water, brine, concentrated in vacuo and the residue chromatographed (4% NH4OH:MeOH:CH2Cl2) to give 540 mg (73%) of (1S,2S,5R)-ethyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)-cyclohexanecarboxylate as a white foam. MS found: (M+H)+=460.51

Workup

  1. stirringstirred at room temperature for 1 h
  2. washwashed with 1 N NaOH, water, brine
  3. concentrationconcentrated in vacuo
  4. customthe residue chromatographed (4% NH4OH:MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-767118094a7e4fd38611ad9d3ed8107a
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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