(2S)-4-aminobutane-1,2-diol → (4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-N-[(3S)-3,4-dihydroxybutyl]-1'-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-4,4-dimethyl-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	(2S)-4-aminobutane-1,2-diol	HCID 55281176	—
Reactant	(3'S,4'R,7'S,8'S,8a'R)-6''-chloro-8'-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3',4'-diphenyl-3',4',8',8a'-tetrahydro-1'H-dispiro[cyclohexane-1,6'-pyrrolo[2,1-c][1,4]oxazine-7',3''-indole]-1',2''(1''H)-dione	HCID 70872025	—
Product	(4'S,5'R)-6''-chloro-4'-(3-chloro-2-fluorophenyl)-N-[(3S)-3,4-dihydroxybutyl]-1'-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-4,4-dimethyl-2''-oxo-1'',2''-dihydrodispiro[cyclohexane-1,2'-pyrrolidine-3',3''-indole]-5'-carboxamide	HCID 68309385	55%

Reaction Steps

The compound (1.01 g, 1.51 mmol) obtained in Step 1 of Example 1 and (2S)-4-aminobutane-1,2-diol (WO2007/011162) (475 mg, 4.53 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 1 to give 644 mg (55%) of the title compound as a colorless amorphous solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08629133B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-0d459261e9584b91bb35e4cefddac3f4
Source note	uspto-grants-2014_01