4-Chlorobenzaldehyde → HCID 66833598, compound

HRID 579553Notes

Reaction equation

HRID 579553 reaction equation
[NH2:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][B:12]1[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:1][CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:19])([CH3:20])[O:13]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66833580HCID 66833580, compound

Product 1

HCID 66833598HCID 66833598, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (119 mg, 0.42 mmol) in 1,2-dichloroethane (1 mL) was treated with 4-chlorobenzaldehyde (89 mg, 0.63 mmol). After stirring for 10 minutes, sodium triacetoxyborohydride (230 mg, 1.05 mmol) was added and stirring was continued for 18 hours. The reaction was diluted with ethyl acetate, washed with saturated aq sodium bicarbonate and sat'd aq sodium chloride, dried over MgSO4, and concentrated. Purification by column chromatography (4-32% ethyl acetate in heptane afford ethyl 2-(4-chlorobenzylamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (59 mg, 34%). Rf 0.28 (20% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 7.29-7.25 (m, 4H), 4.21 (q, J=7.7 Hz, 2H), 3.78, 3.58 (ABq, JAB=13.2 Hz, 2H), 3.20 (t, J=7.0 Hz, 1H), 1.80-1.57 (m, 2H), 1.42-1.34 (m, 4H), 1.30-1.21 (m, 15H), 0.77 (t, J=7.0 Hz, 2H). ESI MS found for C21H33B1Cl1N1O4 m/z [410.1 (M+1)].

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours
  3. washwashed with saturated aq sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by column chromatography (4-32% ethyl acetate in heptane

Sources & evidence

ORD record
ord-e962c4543cc84a0ba0bfc874d5b35510
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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