Sodium borohydride → Ethyl 6,6-Difluoro-7-hydroxy-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 1026447Notes

Reaction equation

[F:1][C:2]1([F:17])[C:10](=[O:11])[C:9]2[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=2[CH2:4][CH2:3]1.[BH4-].[Na+]>C(O)C>[F:17][C:2]1([F:1])[CH:10]([OH:11])[C:9]2[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 5 °C

Procedure

Into a 250-mL 3-necked round-bottom flask was placed a solution of 113j (18 g, 74.01 mmol, 1.00 equiv) in ethanol (100 mL), followed by the addition of NaBH4 (2.8 g, 74.02 mmol, 1.00 equiv) in several batches at 0° C. (FIG. 14). The resulting solution was stirred at 5° C. for 10 min, quenched by the addition of 50 mL of saturated aqueous NH4Cl, concentrated under vacuum and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with 1×100 mL of water and 1×100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 18 g (99%) of 113k as a white solid.

Workup

customInto a 250-mL 3-necked round-bottom flask was placed
customquenched by the addition of 50 mL of saturated aqueous NH4Cl
concentrationconcentrated under vacuum
extractionextracted with 3×50 mL of ethyl acetate
washThe combined organic layers were washed with 1×100 mL of water and 1×100 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ac50066833944dbba9ce5298c7102573
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729072B2

Reaction notes

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