Sodium borohydride → ethyl 2-((3aR,6R,6aR)-6-hydroxyhexahydro-furo[3,2-b]furan-3-yl)acetate
Reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][O:12][C@@H:11]2/[C:14](=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])/[CH2:15][O:16][C@H:10]12)(C(C)(C)C)(C)C.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.C(O)C>[OH:8][C@H:9]1[C@H:10]2[O:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C@H:11]2[O:12][CH2:13]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A 20 mL vessel was charged ethyl(2E)-2-[(3R,3aS,6aR)-3-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-ylidene]acetate (45 mg, 0.137 mmol), nickel chloride hexahydrate (32.6 mg, 0.137 mmol) and ethanol (1 mL). Sodium borohydride (51.8 mg, 1.37 mmol) was added slowly and the mixture was stirred at room temperature for 1 h. The reaction was quenched with water (0.5 mL) and partitioned between water (4 mL) and ethyl acetate (10 mL). The aqueous layer was extracted with ethyl acetate (3×5 mL). The combined organic phases were dried over MgSO4, filtered and concentrated to afford the title compound. LC-MS: calculated for C1OH16O5, [M+Na]+Calc: 239.1. Found: 239.1, Rt=0.22 min (4 min run).
Workup
- customThe reaction was quenched with water (0.5 mL)
- custompartitioned between water (4 mL) and ethyl acetate (10 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (3×5 mL)
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1e1902d9181d46e4b17863ef094c019d
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290517B2
Reaction notes
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