Lithium borohydride → tert-butyl 1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

HRID 1427227Notes

Reaction equation

HRID 1427227 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19](OC)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:18]([N:13]2[C:14]3[C:10](=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)([CH2:23][CH3:24])[CH2:19][OH:20])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70562967methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

Product 1

HCID 70560487tert-butyl 1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[4-(tert-butoxycarbonylamino)-1H-indazol-1-yl]-2-(4-chlorophenyl)butanoate (3.5 g, 7.90 mmol), in THF (140 mL) at 0° C. was added LiBH4 (0.7 g, 31.6 mmol). The mixture was allowed to stir overnight at RT. Then it was quenched with saturated NH4Cl (200 mL) carefully, and extracted with CH2Cl2. The combined organic layers were washed with brine (80 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to afford the desired product. LC/MS m/z=416.3 [M+H]+.

Workup

  1. customThen it was quenched with saturated NH4Cl (200 mL) carefully
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine (80 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6b73678f68e5425db4787d3635728406
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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