Trityl chloride → (s)-2-(Tritylamino)butan-1-ol

HRID 2047648Notes

Reaction equation

HRID 2047648 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].C(N(C(C)C)CC)(C)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>ClCCl.CO.CCOCC>[C:16]([NH:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 8058HexaneHCID 81531DiisopropylethylamineHCID 1200842-Amino-1-butanol, (+)-

Product 1

HCID 57433108(s)-2-(Tritylamino)butan-1-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-(+)-2-aminobutan-1-ol (10 g, 112.18 mmol) in dichloromethane (DCM, 250 ml) under an argon atmosphere at room temperature, was added diisopropylethylamine (DIEA, 19.4 ml, 112.18 mmol) followed by trityl chloride (31.2 g, 112.18 mmol). The reaction mixture was stirred at this temperature for 48 h, when TLC (hexane:ether:MeOH; 55:40:5) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue taken up in ethyl acetate. The organic solution was washed with water (2×), dried over sodium sulphate. The solvent was removed to afford (S)-2-(trityl-amino)-butan-1-ol as a light yellow oil; Yield: 33 g (89%). 1H-NMR (CDCl3, 250 MHz): δ 0.72 (3 H, t, J=7.5 Hz, —NHCH(CH2CH3)CH2OH), 1.15-1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.05 (1 H, s, br, NH), 2.24 (1 H, s, br, OH), 2.62-2.54 (m, 1H, —NHCH(CH2CH3)CH2OH), 3.17-3.08 (1 H m, —NHCH(CH2CH3)CHHOH), 3.35-3.29 (1 H, m, NHCH(CH2CH3)CHHOH), 7.37-7.2 (12H, m, ArH), 7.65-7.58 (3 H, m, ArH); δC (250 MHz, CDCl3) 146.86 (C), 129.43 (6×CH), 127.90 (6×CH), 126.48 (3×CH), 71.27 (C), 62.72 (CH2), 48.91 (CH), 24.55 (CH2), 10.47 (CH3)

Workup

  1. customThe solvent was evaporated in vacuo
  2. washThe organic solution was washed with water (2×)
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-c59470d3513a4e78bf67604790fb459c
Source dataset
uspto-grants-2013_11
Patent number
US08592581B2

Reaction notes

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