Sodium borohydride → [(S)-2-(7-Hydroxymethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

HRID 1453893Notes

Reaction equation

HRID 1453893 reaction equation
C([O:8][C:9]([C:11]1[O:36][C:14]2=[CH:15][CH:16]=[C:17]3[C:21]([N:20]([CH2:22][C@@H:23]([NH:25][C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH3:24])[N:19]=[CH:18]3)=[C:13]2[CH:12]=1)=O)C1C=CC=CC=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C.C1COCC1>[CH2:29]([O:28][C:26](=[O:27])[NH:25][C@@H:23]([CH3:24])[CH2:22][N:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]3[O:36][C:11]([CH2:9][OH:8])=[CH:12][C:13]3=2)[CH:18]=[N:19]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 688563631-((S)-2-Benzyloxycarbonylaminopropyl)-1H-furo[2,3-g]indazole-7-carboxylic acid benzyl ester

Product 1

HCID 68855697[(S)-2-(7-Hydroxymethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl esterYield 49%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from Step A (0.13 g, 0.27 mmol) in ethanol (10 mL) was added calcium chloride (0.06 g, 0.54 mmol) in THF (2 mL) followed by sodium borohydride (0.04 g, 1.07 mmol) at 0° C. and the mixture was stirred at room temperature for 20 h. The reaction mixture was evaporated to a residue and a saturated aqueous solution of ammonium chloride (20 mL was added followed by ethyl acetate (50 mL). The organic layer was separated and the aqueous was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (30 mL), dried and evaporated to a residue, which was purified by chromatography (silica, 50% ethyl acetate in hexane) to give an oil (0.05 g, 49%); MS (ES) m/z 380 (M+).

Workup

  1. customThe reaction mixture was evaporated to a residue
  2. additiona saturated aqueous solution of ammonium chloride (20 mL was added
  3. customThe organic layer was separated
  4. extractionthe aqueous was extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. customdried
  7. customevaporated to a residue, which
  8. customwas purified by chromatography (silica, 50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-da3ddf3c46544befa7a0c89217a3c514
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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