Lithium borohydride → HCID 67271041, compound

HRID 602465Notes

Reaction equation

HRID 602465 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH:25]([CH3:27])[CH3:26])[N:17]=2)=[O:15])[CH2:9][N:8]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])C.[BH4-].[Li+]>O1CCCC1>[OH:3][CH2:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH:25]([CH3:27])[CH3:26])[N:17]=2)=[O:15])[CH2:9][N:8]1[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67270358HCID 67270358, compound

Product 1

HCID 67271041HCID 67271041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl cis-2-(3-ethoxy-3-oxopropyl)-5-{[(1-isopropyl-1H-indazol-3-yl) carbonyl]amino}piperidine-1-carboxylate (300 mg, 0.617 mmol, step 7 of Example 5) in tetrahydrofuran (7 mL) was added at 0° C. a solution of lithium borohydride (2M in tetrahydrofuran, 1.54 mL, 3.08 mmol), and the mixture was stirred at room temperature for 20 h. The mixture was quenched with water (20 mL), extracted with ethyl acetate (30 mL×3). The combined organic layer was washed with brine (20 mL), dried over magnesium sulfate and concentrated under reduced pressure to give 282 mg (quant.) of the title compound as a colorless oil. The resulting residue was used for the next reaction without purification.

Workup

  1. customThe mixture was quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. washThe combined organic layer was washed with brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-726afc994c124e27885f56c00dd40de5
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

Loading…