Acetone → HCID 52913246, compound

HRID 2095571Notes

Reaction equation

HRID 2095571 reaction equation
C[O:2][C:3](=O)[C@@H:4]([N:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:37])[NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[C:28]([Cl:36])[CH:27]=2)[C@@H:20]([CH3:38])[C:19]1=[O:39])[CH2:5][CH2:6][C:7]([N:9]1[CH2:16][CH2:15][C:12]2([CH2:14][CH2:13]2)[C@H:11]([OH:17])[CH2:10]1)=[O:8].[Li+].[BH4-].CO.CC(C)=O>C1COCC1>[Cl:36][C:28]1[CH:27]=[C:26]([NH:25][C:24]([N:21]2[CH2:22][CH2:23][N:18]([C@H:4]([CH2:3][OH:2])[CH2:5][CH2:6][C:7]([N:9]3[CH2:16][CH2:15][C:12]4([CH2:13][CH2:14]4)[C@H:11]([OH:17])[CH2:10]3)=[O:8])[C:19](=[O:39])[C@@H:20]2[CH3:38])=[O:37])[CH:31]=[CH:30][C:29]=1[C:32]([F:33])([F:34])[F:35]

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 4148881Lithium borohydrideHCID 67074676HCID 67074676, compound

Product 1

HCID 52913246HCID 52913246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (−20° C.) solution of 0.29 g (0.50 mmol) of (S)-2-[(S)-4-(3-Chloro-4-trifluoromethyl-phenylcarbamoyl)-3-methyl-2-oxo-piperazin-1-yl]-5-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentanoic acid methyl ester in 1.5 ml of THF was treated with 0.25 ml (0.50 mmol) of LiBH4 (2 M in THF) and 0.04 ml (1.00 mmol) of MeOH in 0.3 ml of THF. The reaction was warmed to +15° C. (during 3 h) and stirred for 1.5 h at RT, cooled to 0° C. and stopped with 0.17 ml (2.28 mmol) of acetone. The reaction was partitioned between aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after flash silica gel column (dichloromethane/MeOH 96:4 to 95:5) and precipitation (dichloromethane/ether) 0.19 g (68%) of the title compound as white amorphous powder. MS: 561.21 (MH+, Cl).

Workup

  1. temperatureThe reaction was warmed to +15° C. (during 3 h)
  2. temperaturecooled to 0° C.
  3. customThe reaction was partitioned between aqueous 10% KHSO4/EtOAc (3×)
  4. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give
  8. customafter flash silica gel column (dichloromethane/MeOH 96:4 to 95:5) and precipitation (dichloromethane/ether) 0.19 g (68%) of the title compound as white amorphous powder

Sources & evidence

ORD record
ord-d98196fdbff748628efd8d521715f2b8
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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