Acetone → HCID 68767605, compound

HRID 1455441Notes

Reaction equation

HRID 1455441 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([C:8]([O:10][CH3:11])=[O:9])[C@@H:5]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[C:13]2=[O:28])[CH2:4][CH2:3]1.[CH3:29][C:30]([CH3:32])=O.[BH-](OC(C)=O)(OC(C)=O)O[C:35](C)=O.[Na+].C=O>C(Cl)Cl>[CH2:21]([O:20][C:18]([NH:17][C@H:14]1[CH2:15][CH2:16][N:12]([C@H:5]2[CH2:4][CH2:3][C@@H:2]([N:1]([CH:30]([CH3:32])[CH3:29])[CH3:35])[CH2:7][C@H:6]2[C:8]([O:10][CH3:11])=[O:9])[C:13]1=[O:28])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68767536HCID 68767536, compound

Product 1

HCID 68767605HCID 68767605, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (1R,2S,5R)-methyl 5-amino-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexanecarboxylate from step 4 (0.75 g, 1.9 mmol) in CH2Cl2 (10 ml) was treated with acetone (1 ml) and NaBH(OAc)3 (0.85 g, 4 mmol) and stired at room temperature for 6 h. A solution of 37% aq formaldehyde (2 ml) was added and stirred at room temperature overnight. The solution was diluted with CH2Cl2 (50 ml) and washed with 1 N NaOH, water, brine, concentrated in vacuo and the residue chromatographed (1:9:90 NH4OH:MeOH:CH2Cl2) to give 0.4 g (50%) of (1R,2S,5R)-methyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)-cyclohexanecarboxylate as a white foam. MS found: (M+H)+=446.3.

Workup

  1. washwashed with 1 N NaOH, water, brine
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed (1:9:90 NH4OH:MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-0309f5b5bb20466b9b22eb186a265cb1
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

Loading…