Sodium borohydride → HCID 86713328, compound

HRID 928001Notes

Reaction equation

HRID 928001 reaction equation
[BH4-].[Na+].FC(F)(F)C([NH:7][C:8]1[C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:16]2[C:11]([CH:12]3[CH2:25][CH:13]3[CH2:14][O:15]2)=[CH:10][CH:9]=1)=O>C(O)C>[NH2:7][C:8]1[C:17]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])=[C:16]2[C:11]([CH:12]3[CH2:25][CH:13]3[CH2:14][O:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86713329HCID 86713329, compound2×

Product 1

HCID 86713328HCID 86713328, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.32 g) was added in portions to a stirred solution of tert-butyl (1aRS,7bSR)-5-(trifluoroacetylamino)-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (Intermediate 123, 0.5 g) in ethanol (20 mL). The resultant mixture was stirred at room temperature for 1 hour then concentrated under vacuum. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether with a gradient of 2-4% to give tert-butyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (0.2 g) as a white solid.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was purified by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and petroleum ether with a gradient of 2-4%

Sources & evidence

ORD record
ord-d6d62857031941e78a8fb016a6b488c7
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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