(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → (3S)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine
Reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)[O:11][CH2:10]1)C1C=CC=CC=1>[Pd]>[CH3:24][C:22]1([CH3:25])[C:21]([CH3:26])([CH3:27])[O:20][B:19]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:17]=2[CH2:18][C@H:9]([NH2:8])[CH2:10][O:11]3)[O:23]1Participants
3
Conditions
- Temperature
- 55 °C
Procedure
The title compound was synthesized as described for Intermediate example I-3 in 67% yield, starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine using 47 w % of 10% palladium on charcoal. The reaction mixture was heated to 55° C. for 1.5 h; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.19 (dd, 1 H), 7.04 (t, 1 H), 6.83 (dd, 1 H), 4.00-4.06 (m, 1 H), 3.50-3.59 (m, 1 H), 3.14-3.23 (m, 1 H), 2.98-3.12 (m, 1 H), 2.52-2.60 (m, 1 H), 1.29 (s, 12 H), 1.06 (s, 2 H); MS (APPI/APCI) m/z 276[M+H+].
Sources & evidence
- ORD record
- ord-f3882125a6cd4a78aaf065f64490b4a7
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143408B2
Reaction notes
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