Sodium Hydroxide → (S)-1'-(tert-butyl)-3-chloro-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 706398Notes

Reaction equation

[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]([CH2:14][C:15]2[C:20]([CH2:21]Cl)=[CH:19][C:18]([Cl:23])=[CH:17][N:16]=2)[C:6]1=[O:24])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C@:7]2([CH2:14][C:15]3=[N:16][CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]3[CH2:21]2)[C:6]1=[O:24])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: -3.299999952316284 °C

Procedure

A solution of 57 (2.39 g, 6.56 mmol) in toluene (50 mL) was cooled to −2.5° C. under nitrogen atmosphere. Compound 61 (17 mg, 0.020 mmol) was charged, and the resulting solution was aged for about 15 min while cooled to −3.3° C. A pre-cooled (−1° C.). aqueous NaOH (26.2 mL, 0.3 N) was charged in over 4 min below −0.6° C. The reaction was aged at −1.3° C. for 3 h. The reaction was quenched with water (10 ml). The organic layer was washed with water (10 mL), concentrated, flushed with IPA to give crude product 58 (2.59 g, 94.4% ee, 83% wt by NMR against 1,3,5-trimethoxybenzene as an internal standard).

Workup

temperatureA pre-cooled (−1° C.)
waitThe reaction was aged at −1.3° C. for 3 h
customThe reaction was quenched with water (10 ml)
washThe organic layer was washed with water (10 mL)
concentrationconcentrated
customflushed with IPA

Sources & evidence

ORD record: ord-866316f4c96149159f8f8ad8fd7738e1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174989B2

Reaction notes

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