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

HRID 81422Notes

Reaction equation

HRID 81422 reaction equation
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].CCN(C(C)C)C(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>C(Cl)Cl.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 27238562-Amino-1-butanol, (-)-

Product 1

HCID 57395035(2R)-2-[(Triphenylmethyl)amino]butan-1-ol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-(−)-2-aminobutan-1-ol (10 g, 1 eq, 112.18 mmol) in DCM (500 mL) under an argon atmosphere at room temperature, was added DIEA (30 mL, 1.54 eq, 172.22 mmol) followed by trityl chloride (35.4 mL, 1.13 eq, 126.98 mmol). The reaction mixture was stirred at room 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 precipitated from acetone (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. Yield: 32 g (86%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.56 (t, 3H, J=7.41 Hz, —NHCH(CH2CH3)CH2OH), 1.10 (m, 2H, —NHCH(CH2CH3)CH2OH), 2.22 (m, 1H, —NHCH(CH2CH3)CH2OH), 2.38 (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×Ph).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue precipitated from acetone (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-4eac02fbddb440a19a7a73549aab61bb
Source dataset
uspto-grants-2014_09
Patent number
US08846696B2

Reaction notes

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