HCID 59281211, compound → [(2R,4R,5S)-5-amino-2-benzyloxymethyl-5-(2-fluorophenyl)tetrahydropyran-4-yl]methanol
Reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[O:18][CH2:17][C@:13]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[NH:14][O:15][CH2:16][C@@H:12]2[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C@]1(C2C=CC(F)=CC=2F)[C@H](CO)CCOC1>>[NH2:14][C@@:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH2:17][O:18][C@@H:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][C@H:12]1[CH2:16][OH:15]Participants
3
Procedure
Compound C14 was prepared from (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(2-fluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C13) according to the general procedure for the synthesis of [(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C11) in Example 1. The product was used directly in the following step. LCMS m/z 346.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.65 (ddd, J=14.0, 4.3, 2.5 Hz, 1H), 2.01-2.14 (m, 1H), 2.32-2.41 (m, 1H), 3.35 (dd, J=11.5, 2.9 Hz, 1H), 3.47-3.61 (m, 3H), 3.66 (dd, J=10.2, 6.6 Hz, 1H), 3.84-3.92 (m, 1H), 4.27 (dd, J=11.5, 2.0 Hz, 1H), 4.61 (AB quartet, JAB=12.1 Hz, ΔνAB=25.1 Hz, 2H), 7.06 (ddd, J=13.0, 8.1, 1.3 Hz, 1H), 7.20-7.26 (m, 1H), 7.28-7.41 (m, 6H), 7.64-7.72 (m, 1H).
Sources & evidence
- ORD record
- ord-bd4135d8df3641f096c665f48309efb9
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933221B2
Reaction notes
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