Iodine → Tert-butyl 5-chlorospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 2190025Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of tert-butyl 5-chloro-2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.530 g, 1.64 mmol) in THF (5 mL) was added NaBH4 (0.311 g, 8.21 mmol). The reaction was cooled to about −20° C. to −10° C. A solution I2 (0.833 g, 3.28 mmol) in THF (3 mL) was added to the mixture dropwise. The reaction was stirred with warming to about room temperature overnight. The reaction was cooled to about 0° C. and quenched by the addition of saturated NH4Cl, and diluted with DCM. The organics were washed with Na2SO3 and brine, dried over MgSO4, filtered and concentrated. The crude residue was purified by column chromatography to yield tert-butyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (0.515 g, 100%). LCMS (APCI+) m/z 209, 211 [M+H-Boc]+; Rt=3.67 min.

Workup

temperatureThe reaction was cooled to about −20° C. to −10° C
temperaturewith warming to about room temperature overnight
customquenched by the addition of saturated NH4Cl
additiondiluted with DCM
washThe organics were washed with Na2SO3 and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by column chromatography

Sources & evidence

ORD record: ord-41a93df37e714b0a834a7c4ea22bbfd3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324221B2

Reaction notes

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