HCID 67073417, compound → HCID 11543824, compound

HRID 2252977Notes

Reaction equation

HRID 2252977 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][CH2:22][CH3:23])=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=2)[CH2:9]1)(OC(C)(C)C)=O>C(O)(C(F)(F)F)=O.ClCCl>[CH2:22]([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:24]([F:25])([F:26])[F:27])[CH3:23]

Participants

4

Reactant 1

HCID 67073417HCID 67073417, compound

Product 1

HCID 11543824HCID 11543824, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-Boc-(R)-2-(4-ethoxy-3-trifluoromethylbenzyl)morpholine, intermediate (a), was dissolved in TFA, (20% v/v solution in dichloromethane, 1.2 mL total) over 3 hrs. The reaction mixture was poured onto an SCX-2 column (2 g) and washed with dichloromethane (2 mL×2) and methanol (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 10 as a yellow oil (17 mg, 85%).

Workup

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

Sources & evidence

ORD record
ord-0b4d05d22efa4e62a98a3201e0ae2d17
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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