Trifluoroacetic acid → HCID 11565325, compound

HRID 2252972Notes

Reaction equation

HRID 2252972 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[CH2:9]1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:16][C:17]=1[C:23]([F:25])([F:26])[F:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67073225HCID 67073225, compound

Product 1

HCID 11565325HCID 11565325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate (a), N-Boc-(R)-2-(4-methoxy-3-trifluoromethylbenzyl)morpholine (23 mg, 0.06 mmol), was deprotected using trifluoroacetic acid, (20% v/v solution in dichloromethane, 1 mL total) over 2.5 hrs. The reaction mixture was poured onto an SCX-2 column (2 g) and washed with dichloromethane (2 mL×2) and dichloromethane: methanol (1:1 v/v, 2 mL×2). The column was then washed with ammonia (2N solution in methanol, 2 mL×3) and the ammonia washes were concentrated in vacuo to yield the desired morpholine, example 2 as a white solid (15 mg, 89%).

Workup

  1. customover 2.5 hrs
  2. additionThe reaction mixture was poured onto an SCX-2 column (2 g)
  3. washwashed with dichloromethane (2 mL×2) and dichloromethane: methanol (1:1 v/v, 2 mL×2)
  4. washThe column was then washed with ammonia (2N solution in methanol, 2 mL×3)
  5. concentrationthe ammonia washes were concentrated in vacuo

Sources & evidence

ORD record
ord-c61a839ad1ff43de8f0bc7ecbf6b6733
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

Loading…