Acetic Acid → 6-((4-(Prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid

HRID 1052314Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:10]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[C:11]#[CH:12].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O>[CH2:10]([O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[CH:20][CH:21]=1)[C:11]#[CH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-aminohexanoic acid (2.62 g, 20 mmol), 4-(prop-2-yn-1-yloxy)benzaldehyde (0.80 g, 5.0 mmol) and acetic acid (0.50 mL) in DCE (50 mL) was heated at 80° C. for 60 min. The reaction mixture was cooled to 0° C., and treated with NaBH(OAc)3 (2.11 g, 10 mmol). The reaction was stirred at room temperature for 12 hours and decomposed with water and then extracted with DCM. The organic layer was dried and concentrated under reduced pressure to give a residue, which was purified using a Biotage SP4 and gradient elution of 5-50% methanol in DCM. The yield of the target compound 6-((4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid was 62% (0.856 g). 1H NMR (400 MHz, DMSO-d6): δ 7.19 (d, J=8.4 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.71 (s, 2H), 3.56 (s, 2H), 3.49 (s, 1H), 2.39 (t, J=7.0 Hz, 2H), 2.00 (t, J=7.2 Hz, 2H), 1.41-1.19 (m, 6H); MS (ESI), 276.1 (M+H)+.

Workup

extractionextracted with DCM
customThe organic layer was dried
concentrationconcentrated under reduced pressure
customto give a residue, which
customwas purified
washa Biotage SP4 and gradient elution of 5-50% methanol in DCM

Sources & evidence

ORD record: ord-50f2d53bc4b6499db8c2f7b5ab60c96f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388144B2

Reaction notes

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