Triethylamine → (2s)-Methyl 2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylamino)-4-methylpentanoate

HRID 1040286Notes

Reaction equation

HRID 1040286 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH3:18][C:19]1([CH3:28])[CH:24]2[CH2:25][CH:20]1[CH2:21][CH:22]=[C:23]2[CH:26]=O.CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH3:18][C:19]1([CH3:28])[CH:24]2[CH2:25][CH:20]1[CH2:21][CH:22]=[C:23]2[CH2:26][NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 61130MyrtenalHCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 68939080(2s)-Methyl 2-((6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methylamino)-4-methylpentanoateYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-leucine methyl ester hydrochloride (2.0 gm, 11.0 mmol), THF (25 mL), MgSO4 (2.24 gm, 18.7 mmol), (1R)-(−) myrtenal (3.30 g, 22.0 mmol), Et3N (1.54 mL, 11.0 mmol), sodium borohydride (832 mg, 22.0 mmol), and methanol (20 mL) to give 11l (1.56 gm, 51%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.82 (3H, s), 0.89 (3H, d, J=6.59 Hz), 0.91 (3H d, J=6.83 Hz), 1.15 (1H, d, J=8.54 Hz), 1.27 (3H, s), 1.38-1.54 (3H, m), 1.68 (1H, m), 2.08 (2H, d, J=5.37 Hz), 2.24 (2H, q, J=16.11 Hz), 2.32-2.4 (1H, m), 2.94 (1H, dd, J=1.7, 13.91 Hz), 3.08 (1H, dd, J=1.46, 13.67 Hz), 3.29 (1H, t, J=7.32 Hz), 3.71 (3H, s), 5.36 (1H, s). ESI-MS: 302.2 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-07feb3c99b954f3b84fac0d725713ba7
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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