Triethylamine → HCID 86587177, compound

HRID 1611915Notes

Reaction equation

HRID 1611915 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]([NH2:10])[C@@H:2]1[OH:11].C(N(CC)CC)C.[C:19](Cl)(=[O:23])[CH2:20][CH2:21][CH3:22]>C1COCC1>[OH:11][C@@H:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]1[NH:10][C:19](=[O:23])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Product 1

HCID 86587177HCID 86587177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(1S, 2R)-cis-1-Amino-2-indanol (XIV, 1.5 g) was dissolved with triethylamine (1.5 mL) in dry THF (45 mL), and cooled to 0° C. Butyryl chloride (XIII, 1.05 mL) was added by syringe, and the resultant solution stirred 0° C. for 20 min, whereupon the reaction mixture was partitioned between half-saturated NH4Cl (45 mL) and EtOAc (2×45 mL). The combined organic layers were dried dried (MgSO4), filtered, and concentrated under reduced pressure to give a solid, which was taken to the next reaction without further purification.

Workup

  1. customwas partitioned between half-saturated NH4Cl (45 mL) and EtOAc (2×45 mL)
  2. customThe combined organic layers were dried
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a solid, which
  7. customwas taken to the next reaction without further purification

Sources & evidence

ORD record
ord-8b5636cc7cc04d849b8fd6e703d3b4e4
Source dataset
uspto-grants-2006_01
Patent number
US06992081B2

Reaction notes

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