Triethylamine → HCID 56991025, compound

HRID 414574Notes

Reaction equation

HRID 414574 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C@@H:10]1[C@@H:15]([NH2:16])[CH2:14][C@H:13]2[CH2:17][C@@H:11]1[C:12]2([CH3:19])[CH3:18].C(N(CC)CC)C.[C:27](Cl)(=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C@@H:10]1[C@@H:15]([NH:16][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:14][C@H:13]2[CH2:17][C@@H:11]1[C:12]2([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 14352646HCID 14352646, compound

Product 1

HCID 56991025HCID 56991025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a atmosphere of argon, to a mixture of (1S,2S, 3S,5R)-10-(tetrahydropyran-2-yloxy)methylpinan-3-ylamine (20 g; prepared in reference example 8), triethylamine (25 ml) and anhydrous tetrahydrofuran (200 ml), a solution of caproyl chloride (13 ml) in anhydrous tetrahydrofuran (30 ml) was dropped and the mixture was stirred for 2 hrs at room temperature. The diluted solution with diethyl ether was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulphate and then concentrated under reduced pressure to give the title compound (28 g) having the following physical data:

Workup

  1. washThe diluted solution with diethyl ether was washed with water
  2. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e18e6ee2c634e7196bd89c22344686e
Source dataset
uspto-grants-1988_12
Patent number
US04792550

Reaction notes

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