Hydrochloric Acid → HCID 86701854, compound

HRID 1844093Notes

Reaction equation

HRID 1844093 reaction equation
[O:1]=[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]2[C:14]3[C:19]([C:20](=[O:21])[C@@H:4]2[CH2:3]1)=[CH:18][CH:17]=[CH:16][CH:15]=3.[BH4-].[Na+].Cl>C(O)C.C1COCC1>[OH:21][C@@H:20]1[C@H:4]2[C@H:5]([N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:2](=[O:1])[CH2:3]2)[C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86701853HCID 86701853, compound2×

Product 1

HCID 86701854HCID 86701854, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (3aR,8bS)-2,4-dioxo-3a,8b-dihydro-3H-indeno[1,2-b]pyrrole-1-carboxylate F 26 (1.60 g, 5.56 mmol) in ethanol (20 mL) and THF (20 mL) was added at 0° C. NaBH4 (0.316 g, 8.15 mmol). The solution was stirred for 2 h at 0° C. 1M HCl was carefully added and the solution was concentrated in vacuo. The residue was partitioned between ethyl acetate and water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography (2/1 cyclohexane/ethyl acetate) to give tert-butyl (3aR,4R,8bS)-4-hydroxy-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate F27 (800 mg, 50%). LCMS (method E): 0.78 min; ES+: 601 (2M+Na+).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (2/1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-631100621196410e85c6b92afc5f1f7d
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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