(R)-Tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-YL)carbamate → 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine

HRID 870949Notes

Reaction equation

HRID 870949 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH:9]([CH3:16])[O:8][C:6]=2[CH:7]=1.[F:17][C:18]([CH3:32])([CH3:31])[CH2:19][CH:20]([NH:23]C(=O)OC(C)(C)C)[CH2:21][OH:22]>>[F:17][C:18]([CH3:32])([CH3:31])[CH2:19][CH:20]([NH2:23])[CH2:21][O:22][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[CH:9]([CH3:16])[O:8][C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 78166485(R)-Tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-YL)carbamateHCID 866958958-chloro-5-methyl-5H-chromeno[3,4-c]pyridine

Product 1

HCID 717267684-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amineYield 99%

Procedure

Prepared as described in Example 8, Part D using 8-chloro-5-methyl-5H-chromeno[3,4-c]pyridine (0.100 g, 0.432 mmol) and tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-yl)carbamate (0.168 g, 0.712 mmol) to afford 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine (80 mg, 0.23 mmol, 99% yield) as a yellow oil. 1H NMR (400 MHz, MeOD) δ 8.66 (d, J=6.4 Hz, 1H), 8.64 (s, 1H), 8.24 (d, J=6.4 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 6.94 (dd, J=2.4 Hz, 8.8 Hz, 1H), 6.78 (d, J=2.8 Hz, 1H), 5.57 (q, J=6.4 Hz, 1H), 4.38 (dd, J=6.4 Hz, J=10.8 Hz, 1H), 4.22 (dd, J=6.4 Hz, 10.8 Hz, 1H), 3.99 (m, 1H), 2.16 (m, 2H), 1.75 (d, J=6.8 Hz, 3H), 1.55 (s, 3H), 1.50 (s, 3H); LCMS (ESI) m/e 331.2 [(M+H)1, calcd for C19H24FN2O2 331.2] LC/MS retention time (method D): tR=0.97 min; HPLC retention time (method B): tR=8.04 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a63dd130399f4a2a9734cd176cb3fa05
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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