1,2,2,3-Tetramethylpiperidine → HCID 69060564, compound

HRID 1432823Notes

Reaction equation

HRID 1432823 reaction equation
[CH3:1]C1CCCN(C)C1(C)C.C([Li])CCC.[CH:16]1([CH2:19][CH:20]=[CH:21][CH2:22][CH:23]2[CH2:25][O:24]2)[CH2:18][CH2:17]1>CC(OC)(C)C>[CH:16]1([CH2:19][CH:20]2[CH:22]3[CH:21]2[CH2:1][CH2:25][CH:23]3[OH:24])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 187617721,2,2,3-TetramethylpiperidineHCID 86607686HCID 86607686, compoundHCID 178418339Butyllithium

Product 1

HCID 69060564HCID 69060564, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tetramethylpiperidine (0.624 ml, 3.7 mmol) in MTBE (5 mL) was added n-butyllithium 2.5M hexanes (1.5 ml, 3.7 mmol) at −78° C. The solution was slowly warmed to approx 0° C. and was added via cannula to a solution of 2-(4-cyclopropyl-but-2-enyl)-oxirane (0.288 g, 1.898 mmol) in MTBE (2 mL) over 10 min at 0° C. The mixture was allowed to warm to rt, stirred overnight, washed with 1N HCl (2×), and brine. The organics were dried over MgSO4, filtered, and concentrated to give 6-cyclopropylmethyl-bicyclo[3.1.0]hexan-2-ol as clear oil; 1H NMR(400 MHz, CDCl3): δ 4.19 (d, 1H, J=5.5 Hz), 2.15-2.06 (m, 1H), 1.75 (dd, 1H, J1=11.0 Hz, J2=9.7 Hz), 1.69-1.52(m, 4H), 1.42 (dd, 1H, J1=8.1 Hz, J2=6.2 Hz), 0.98-0.87 (m, 2H), 0.75-0.68 (m, 1H), 0.46-0.41 (m, 2H), 0.03 (dd, 2H, J1=9.1 Hz, J2=4.7 Hz).

Workup

  1. temperatureto warm to rt
  2. washwashed with 1N HCl (2×), and brine
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c4a0c554a2474a74841adec012428fa3
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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