HCID 178501239, compound → HCID 178453956, compound

HRID 928233Notes

Reaction equation

HRID 928233 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:16][CH2:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:14][CH2:13]1

Participants

3

Reactant 1

HCID 178501239HCID 178501239, compound

Product 1

HCID 178453956HCID 178453956, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-methyl 4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (9.0 g, 35 mmol) in THF (70 mL) was added slowly a 2.0 M solution of LiAH4 in THF (20 mL, mmol) at −78° C. The reaction was warmed slowly to room temperature (over 4 h), and quenched by dropwise addition of water (5 mL), followed by addition of NaOH (5 mL) and Na2SO4. The mixture was stirred for 20 min and filtered. The filtrate was dried (Na2SO4), and concentrated. The crude mixture was purified by Isco to provide tert-butyl trans-4-(hydroxymethyl)cyclohexylcarbamate (5.5 g, 69%) as a white solid.

Workup

  1. customquenched by dropwise addition of water (5 mL)
  2. additionfollowed by addition of NaOH (5 mL) and Na2SO4
  3. filtrationfiltered
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude mixture was purified by Isco

Sources & evidence

ORD record
ord-e254e2e0ac8c41e4b5db3696e7fcd561
Source dataset
uspto-grants-2016_03
Patent number
US09290499B2

Reaction notes

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