Aluminium lithium hydride → 4-(Methylamino)tricyclo[3.3.1.13,7]decan-1-ol

HRID 2407367Notes

Reaction equation

HRID 2407367 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12](=O)[NH:13][CH:14]1[CH:21]2[CH2:22][CH:17]3[CH2:18][C:19]([OH:24])([CH2:23][CH:15]1[CH2:16]3)[CH2:20]2)(C)(C)C>C1COCC1>[CH3:12][NH:13][CH:14]1[CH:21]2[CH2:22][CH:17]3[CH2:18][C:19]([OH:24])([CH2:23][CH:15]1[CH2:16]3)[CH2:20]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59226759HCID 59226759, compound

Product 1

HCID 37214804-(Methylamino)tricyclo[3.3.1.13,7]decan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (0.711 g, 0.018 mol) was added to a solution of (5-hydroxy-adamantan-2-yl)carbamic acid tert-butyl ester (1 g, 0.0037 mol) in THF (50 ml) at 0° C. under a nitrogen atmosphere. The slurry was heated under reflux for 5 h. It was then cooled to 0° C. and quenched with 30% NaOH solution (12 ml) and filtered. The filtrate was concentrated to give 2-methylaminoadamantan-5-ol as a white solid (0.6 g, 90%). LC-MS (m/z): 181.9 (M+1). 1H NMR (300 MHz, DMSO-d6): δ 4.3 (s, 1H), 4.2 (s, 1H), 2.4 (s, 0.7H), 2.3 (s, 0.3H), 2.2 (s, 3H), 1.8-2.0 (m, 5H), 1.5-1.6 (m, 5H), 1.4-1.5 (m, 2H), 1.2 (m, 2H).

Workup

  1. temperatureThe slurry was heated
  2. temperatureunder reflux for 5 h
  3. customquenched with 30% NaOH solution (12 ml)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-99c56e4c9f8046e2ab6d2a4b8c5f22bf
Source dataset
uspto-grants-2014_08
Patent number
US08809540B2

Reaction notes

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