Morpholine → HCID 18388363, compound

HRID 842217Notes

Reaction equation

HRID 842217 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH:18]=O)[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([CH2:18][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:15]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 18723527HCID 18723527, compound

Product 1

HCID 18388363HCID 18388363, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.03 g (0.073 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-formylpyrrolidine and 0.013 mL (0.145 mmol) of morpholine in 2 mL of dichloroethane at rt was added 0.046 g (0.27 mmol) of sodium triacetoxyborohydride. After stirring for 1.5 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, CH2Cl2:MeOH, 95:5) to give the title compound. 1H NMR (CDCl3) δ (complete) 7.87-7.90 (m, 3H), 7.45-7.55 (m, 4H), 7.17-7.20, 7.08-7.11 (m, 2H), 7.00, 6.95 (t, 2H, J=9.0 Hz),4.03-4.09 (m, 1H), 3.72 (t, 2H, <J=4.5 Hz), 3.60-3.64 (m, 1H), 3.56 (t, 2H, J=4.5 Hz), 2.97-3.06 (m, 2H), 2.82-2.88 (m, 1H), 2.43-2.55 (m, 4H), 2.24-2.43 (m, 5H), 2.09-2.19 (m, 3H), 1.49-1.98 (m, 5H); Mass Spectrum (ESI) m/e=516 (M+1).

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, CH2Cl2:MeOH, 95:5)

Sources & evidence

ORD record
ord-21e1fcf157724ab2abada1170b4c5547
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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