HCID 71059906, compound → HCID 71059530, compound

HRID 1525166Notes

Reaction equation

HRID 1525166 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C@:5]2([NH:22][S@@](C(C)(C)C)=O)[C:17]([F:21])([F:20])[CH2:18][OH:19]>CCCCCCC.C(OCC)(=O)C>[NH2:22][C@@:5]1([C:17]([F:21])([F:20])[CH2:18][OH:19])[C:4]2[C:14](=[CH:15][CH:16]=[C:2]([Br:1])[CH:3]=2)[O:13][C@:7]2([CH2:12][CH2:11][CH2:10][O:9][CH2:8]2)[CH2:6]1

Participants

3

Reactant 1

HCID 71059906HCID 71059906, compound

Product 1

HCID 71059530HCID 71059530, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

Starting from (R)—N-((4R)-6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2-methylpropane-2-sulfinamide (intermediate B4.7), and after chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to =:100 as the eluent the 2-((2R,4R)-4-amino-6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2,2-difluoroethanol (47% yield) (intermediate B5.7A) was obtained as the first eluting isomer as a white foam; MS (ISP): m/z=378.0 [M+H]+ and 380.0 [M+2+H]+. The second eluting isomer, 2-((2S,4R)-4-amino-6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)-2,2-difluoro ethanol (27% yield) (intermediate B5.7B) was also obtained as a white foam; MS (ISP): m/z=378.0 [M+H]+ and 380.0 [M+2+H]+.

Sources & evidence

ORD record
ord-6cbc0ddeb89b41b9bd005dba835eaa70
Source dataset
uspto-grants-2015_07
Patent number
US09079919B2

Reaction notes

Loading…