Triethylamine → tert-Butyl (4-hydroxybutyl)(methyl)carbamate

HRID 565408Notes

Reaction equation

HRID 565408 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[CH3:15][C:16]([O:19][C:20]([O:22]N=C(C1C=CC=CC=1)C#N)=O)([CH3:18])[CH3:17]>O1CCOCC1>[C:20]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7])([O:19][C:16]([CH3:15])([CH3:17])[CH3:18])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2×HCID 98339374-(Methylamino)butan-1-ol

Product 1

HCID 14854943tert-Butyl (4-hydroxybutyl)(methyl)carbamateYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile. The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane, then with 40% ethyl acetate/hexane, and finally with 75% ethyl/hexane. The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84%): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm.

Workup

  1. concentrationconcentrated via rotary evaporation
  2. customThe residue was chromatographed on silica gel
  3. washeluting first with 20% ethyl acetate/hexane
  4. additionThe fractions containing product
  5. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-eb5dd66b0c6c4c45a97f5b2c0918543b
Source dataset
uspto-grants-2001_01
Patent number
US06172045B2

Reaction notes

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