Methanol → (2R)-2-[(Triphenylmethyl)amino]butan-1-ol

HRID 1432387

Reaction equation

HRID 1432387 reaction equation
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCCCCC.CO>C(Cl)Cl>[C:7]([NH:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6456Trityl chlorideHCID 8058HexaneHCID 27238562-Amino-1-butanol, (-)-

Product 1

HCID 57395035(2R)-2-[(Triphenylmethyl)amino]butan-1-olYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-(−)-2-aminobutan-1-ol (10 g, 112.18 mmol) in CH2Cl2 (500 mL) under Ar at RT, was added Pri2NEt (30 mL, 172.22 mmol) followed by trityl chloride (35.4 mL, 126.98 mmol). The reaction mixture was stirred at RT for 48 h, when TLC (55:40:5 hexane/Et20/MeOH) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue precipitated from Me2CO (50 mL) with hexane (900 mL) with stirring, the precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in hexane (1 L), filtered, and the filtrate was evaporated in vacuo to afford the title compound as a light yellow oil (32 g, 86%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.56 (t, 3H, J=7.41, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.21 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.72+3.00 (2×m, 2H, —NHCH(CH2CH3)CH2OH), 4.28 (t, 1H, J=5.26 Hz, —NHCH(CH2CH3)CH2OH), 7.14-7.49 (m, 15H, 3×Bz).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue precipitated from Me2CO (50 mL) with hexane (900 mL)
  3. stirringwith stirring
  4. customthe precipitate was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe residue was dissolved in hexane (1 L)
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-2d0a4f561e684b1fb0a8ceacb975eba2
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Linked notes

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