Methanol → 2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]acetaldehyde

HRID 626483Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C@@:16]1([CH2:26][C:27]#N)[CH2:25][C:20]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1.C[OH:30].O>C1(C)C=CC=CC=1>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C@@:16]1([CH2:26][CH:27]=[O:30])[CH2:25][C:20]2([CH2:24][CH2:23][CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: -78 °C

Procedure

1.0 M DIBAL solution in toluene (3.0 ml, 3 mmol) was added drop-wise to a solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetonitrile (350 mg, 1.4 mmol) in 7 mL toluene at −78° C. The resulting mixture was stirred at −78° C. until completion (1.5 h). The reaction was then quenched with 5 eq of MeOH (0.28 mL) and 0.1 mL water, stir while warming, 175 mg NA2SO4 added, stir at room temp. 2 h to give 310 mg (80%) of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde. LCMS m/z 250.6 (M+1) observed.

Workup

stirringstir
temperaturewhile warming
addition175 mg NA2SO4 added
stirringstir at room temp

Sources & evidence

ORD record: ord-293cb09e79a240bbb3a414d2d79a49d3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309234B2

Reaction notes

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