HCID 19021731, compound → HCID 10421359, compound

HRID 1109075Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15](=O)[CH2:16][C:17]([CH3:22])([CH3:21])[CH2:18][CH2:19][OH:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>O1CCCC1>[CH2:7]([NH:14][CH2:15][CH2:16][C:17]([CH3:21])([CH3:22])[CH2:18][CH2:19][OH:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Part B. A slurry of lithium aluminum hydride (5.50 g, 145 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., and a solution of the amide prepared in Part A (11.48 g, 47.2 mmol) in tetrahydrofuran (50 mL) was added dropwise over 1 hour. The ice bath was removed, and the mixture was heated to reflux for 18 hours. After cooling to 0° C., the mixture was quenched by the slow dropwise addition of water (6 mL), aq. NaOH (18 mL, 15%), and water (18 mL). The solution was filtered through a plug of Celite®, dried over potassium carbonate, and concentrated under vacuum to afford N-heptyl-3,3-dimethyl-5-hydroxypentanamine as a clear, colorless oil (7.61 g, 33.2 mmol, 70%). 1H NMR (CDCl3) δ 3.70(dt,2H,J=10.2,7.0 Hz); 2.70-2.55(m,2H); 2.39-2.29(m,2H); 1.56(dt,2H,J=12-1,7.0 Hz); 1.51-1.41(m,6H); 1.36-1.24(m,8H); 0.91(s,6H); 0.88(t,3H, J=6.9 Hz).

Workup

additionwas added dropwise over 1 hour
customThe ice bath was removed
temperaturethe mixture was heated
temperatureto reflux for 18 hours
customthe mixture was quenched by the slow dropwise addition of water (6 mL), aq. NaOH (18 mL, 15%), and water (18 mL)
filtrationThe solution was filtered through a plug of Celite®
dry with materialdried over potassium carbonate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-ddff055c93314b2fb533e9afbe4dbd67
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05318984

Reaction notes

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