Hydrochloric Acid → HCID 69917655, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Diethyl Ether	HCID 3283	—
Reactant	Aluminium lithium hydride	HCID 21226445	—
Reactant	(2s)-2-Tert-butoxycarbonylamino-3-[5-(tert-butyl-dimethyl-silanyloxy)-1h-indol-3-yl]-propionic acid methyl ester	HCID 69918141	—
Solvent	Methanol	HCID 887	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 69917655	HCID 69917655	70.7%

Reaction Steps

To a solution of Example 400B (1.50 g, 3.3 mmol) in THF (15 mL) was slowly added LiAlH4 powder (127 mg, 3.3 mmol) in several portion at rt. After the addition, the reaction mixture was becoming sticky and the stirring stopped. The temperature of the mixture arises to ˜50° C. Ether (30 mL) was added and the mixture was stirred for 20 min. Methanol (2 mL) and diluted HCl was added slowly and the mixture was extracted with ether. The organic phase was washed with water and concentrated. The residue was separated by flash chromatography (20-60% EtOAc in hexane) to give the desired product (982 mg, 70%). MS (DCI) m/z 421 (M+1)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06831175B2
Source dataset	uspto-grants-2004_12
ORD ID	ord-45b8c9c878eb43e2b8c8e962beb65458
Source note	uspto-grants-2004_12