(3R,4R)-3-methylpiperidin-4-yl pivalate → (3R,4R)-4-Methoxy-3-methylpiperidine

HRID 80751Notes

Reaction equation

HRID 80751 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@@H:4]1[CH3:9].C(O[C@@H]1CCNC[C@H]1C)(=O)C(C)(C)C>>[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][NH:6][CH2:5][C@H:4]1[CH3:9]

Participants

3

Reactant 2

HCID 59600263(3R,4R)-3-methylpiperidin-4-yl pivalateHCID 86327678(3S,4S)-4-methoxy-3-methylpiperidine

Product 1

HCID 86327680(3R,4R)-4-Methoxy-3-methylpiperidine

Procedure

The same procedures employed to synthesize (3S,4S)-4-methoxy-3-methylpiperidine Examples 9-C were utilized, however the starting material used was (3R,4R)-3-methylpiperidin-4-yl pivalate (CAS#863249-35-8, prepared as described in WO 2005077932). 1H NMR (400 MHz, CD2Cl2) δ ppm 0.92 (d, J=6.6 Hz, 3 H) 1.22 (tdd, J=12.3, 12.3, 10.4, 4.3 Hz, 1 H) 1.39-1.55 (m, 1 H) 2.04 (dq, J=12.4, 3.5 Hz, 1 H) 2.23 (dd, J=12.6, 10.6 Hz, 1 H) 2.55 (td, J=12.4, 2.8 Hz, 1 H) 2.75 (td, J=9.7, 4.2 Hz, 1 H) 2.96 (ddd, J=12.6, 4.2, 1.4 Hz, 1 H) 3.02-3.11 (m, 1 H) 3.31 (s, 3 H).

Sources & evidence

ORD record
ord-58ce7a0f271a4c83a24cac649772753d
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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