1-Pyrrolidinecarboxylate → 1-((2R,3R,4R)-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]-ethoxy}tetrahydro-3-phenyl-2H-pyran-4-yl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

HRID 747037Notes

Reaction equation

[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:20]([C@H:28]3CCN3C)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N:35]1([C:40]([O-:42])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36]1>>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:20]([CH:28]3[O:41][C:40](=[O:42])[N:35]4[CH2:39][CH2:38][CH2:37][CH:36]34)[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:4]=[C:3]([C:2]([F:34])([F:33])[F:1])[CH:8]=1

Participants

Reactant 2

HCID 223251731-Pyrrolidinecarboxylate

HCID 86606931(2R)-2-((2R,3R,4R)-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy}-tetrahydro-3-phenyl-2H-pyran-4-yl)-1-methylazetidine

Product 1

HCID 866069301-((2R,3R,4R)-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]-ethoxy}tetrahydro-3-phenyl-2H-pyran-4-yl)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Procedure

Prepared from (2R or S)-2-[(R or S)-((2R,3R,4R)-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}tetrahydro-3-phenyl-2H-pyran-4-yl)hydroxymethyl]-1-pyrrolidinecarboxylate (Example 41, Isomer B) according to the method of Example 42.

Sources & evidence

ORD record: ord-bbf9f1b8017b440d983ab22d92ddef9b
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393858B2

Reaction notes

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