Beta-Aminoisobutyric Acid → Tert-butyl 5-formyl-6-azaspiro[2.5]octane-6-carboxylate

HRID 536586

Reaction equation

HRID 536586 reaction equation
[OH:1][CH2:2][C@H:3]1[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:8][C:5]2([CH2:7][CH2:6]2)[CH2:4]1.CC1(C)N([O])C(C)(C)CCC1.CC(C(O)=O)CN>C(Cl)Cl>[CH:2]([CH:3]1[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:8][C:5]2([CH2:6][CH2:7]2)[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 64956Beta-Aminoisobutyric AcidHCID 2724126TempoHCID 66848101(S)-tert-butyl 5-(hydroxymethyl)-6-azaspiro[2.5]octane-6-carboxylate2×

Product 1

HCID 86664865Tert-butyl 5-formyl-6-azaspiro[2.5]octane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (S)-tert-butyl 5-(hydroxymethyl)-6-azaspiro[2.5]octane-6-carboxylate (Intermediate 18, 20 g, 82.0 mmol) dissolved in 80 ml of DCM, TEMPO (2.6 g, 16 mmol) and BAIB (29.3 g, 90 mmol) were added. After 2 hours at 25° C., the reaction is diluted with DCM (150 ml), washed with an aqueous solution of Na2S2O3 then with water, dried (Na2SO4) and evaporated to obtain a crude that was purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5). (S) tert-butyl 5-formyl-6-azaspiro[2.5]octane-6-carboxylate was obtained as light yellow solid (7 g).

Workup

  1. washwashed with an aqueous solution of Na2S2O3
  2. dry with materialwith water, dried (Na2SO4)
  3. customevaporated
  4. customto obtain a crude that
  5. customwas purified by silica gel chromatography (petroleum ether to petroleum ether/ethylacetate 95/5)

Sources & evidence

ORD record
ord-886c91a01a774264bc970b03120f5cb6
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Linked notes

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