Hydrochloric Acid → (S)-3-hydroxy-pyrrolidine-1-carboxylic acid 5-hydroxy-adamantan-2-yl ester

HRID 1752309

Reaction equation

ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[C:13]12([OH:24])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15](C3O)[CH2:14]1)[CH2:20]2.[OH:25][C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1.Cl>ClCCl.N1C=CC=CC=1>[OH:24][C:13]12[CH2:14][CH:15]3[CH2:21][CH:19]([CH2:18][CH:17]([CH:7]3[O:6][C:5]([N:28]3[CH2:29][CH2:30][C@H:26]([OH:25])[CH2:27]3)=[O:11])[CH2:22]1)[CH2:20]2

Participants

Conditions

Temperature: -10 °C

Procedure

Triphosgene (0.58 g) dissolved in dichloromethane (10 mL) is added dropwise to a solution of adamantane-1,4-diol (1.00 g) and pyridine (10 mL) in dichloromethane (30 mL) cooled to −10° C. The solution is stirred at ca. 0° C. for 2.5 h and then (S)-3-hydroxy-pyrrolidine (0.50 mL) is added. The resulting solution is stirred overnight while warming to room temperature. The solution is then diluted with dichloromethane (50 mL) and chilled in an ice bath. 4 M hydrochloric acid (25 mL) is added and the resulting mixture is stirred for 5 min. The organic phase is separated and washed with 4 M hydrochloric acid and water. The organic phase is dried (MgSO4) and concentrated to give the title compound as a mixture of diastereomers (ca. 1:1). Yield: 0.98 g (59% of theory); Mass spectrum (ESI+): m/z=282 [M+H]+.

Workup

stirringThe resulting solution is stirred overnight
temperaturewhile warming to room temperature
temperaturechilled in an ice bath
stirringthe resulting mixture is stirred for 5 min
customThe organic phase is separated
washwashed with 4 M hydrochloric acid and water
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-aa4f94b162ee4f46bfbaeb81dc283bc1
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163012B2

Linked notes

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