Methanol → HCID 178520922, compound

HRID 1909494Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.ClC1C=CC([C@H]2CC[C@H](C(O)=O)CC2)=CC=1.CO.[S:34](S([O-])=O)([O-:37])(=[O:36])=[O:35].[Na+].[Na+]>CCOC(C)=O.O>[S:34](=[O:35])([OH:37])[OH:36].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH:14]=[O:15])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 51 °C

Procedure

A stirred solution of trans-4-(4-chlorophenyl)cyclohexanecarbaldehyde (compound of formula (IVa) (approximately 9.33 g, 41.9 mmol, assuming quantitative conversion for preparation from trans-4-(4-chlorophenyl)cyclohexanecarboxylic acid) in EtOAc (100 mL) was charged with MeOH (40 mL), water (10 mL) and sodium metabisulfite (4.38 g, 0.55 eq). The resulting slurry was heated to 51° C., and stirred at this temperature for 45 min, the slurry was cooled to 20° C. over 1 hr then held for 30 min. The slurry was filtered and the cake washed with EtOAc (2×20 mL). The product was de-liquored then dried further in a 45° C. oven under reduced pressure to yield the title compound as a colourless solid (11.04 g, 81%). 1H NMR (400 MHz, d6-DMSO) δH 1.10-1.43 (4H, m, CH-alkyl), 1.70-1.80 (3H, m, CH-alkyl), 1.87-1.94 (1H, m, CH-alkyl), 2.12-2.21 (1H, m, CH-alkyl) 2.37-2.47 (1H, m, OH), 3.67 (1H, m, H-6), 4.79 (1H, m, H-9), 7.20-7.34 (4H, m, H-1 and H-2).

Workup

temperaturethe slurry was cooled to 20° C. over 1 hr
waitthen held for 30 min
filtrationThe slurry was filtered
washthe cake washed with EtOAc (2×20 mL)
customThe product was de-liquored then dried further in a 45° C. oven under reduced pressure

Sources & evidence

ORD record: ord-b60b753c8a13408a8553d3c2fdb463bd
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598387B2

Reaction notes

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